Trifluoroacetic acid → HCID 57567368, compound

HRID 1915441Notes

Reaction equation

HRID 1915441 reaction equation
C(OC([NH:8][CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]3[C:31](=[O:32])[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)=[O:21])[CH:17]=2)[CH2:12][CH2:11][CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]3[C:31](=[O:32])[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)=[O:21])[CH:17]=2)[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59687316[7-[(4-oxo-1H-quinolin-3-yl)carbonylamino]tetralin-1-yl]aminoformic acid tert-butyl ester

Product 1

HCID 57567368HCID 57567368, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [7-[(4-oxo-1H-quinolin-3-yl)carbonylamino]tetralin-1-yl]aminoformic acid tert-butyl ester (273) (250 mg, 0.6 mmol) in dichloromethane (2 mL) was added TFA (2 mL). The reaction was stirred at room temperature for 30 min. More dichloromethane (10 mL) was added to the reaction mixture and the solution was washed with sat. NaHCO3 solution (5 mL). A precipitate began to form in the organic layer so the combined organic layers were concentrated to yield N-(1-aminotetralin-7-yl)-4-oxo-1H-quinoline-3-carboxamide (273-I) (185 mg, 93%). HPLC ret. time 1.94 min, 10-99% CH3CN, 5 min run; ESI-MS 334.5 m/z (MH+).

Workup

  1. washthe solution was washed with sat. NaHCO3 solution (5 mL)
  2. customto form in the organic layer so the combined organic layers
  3. concentrationwere concentrated

Sources & evidence

ORD record
ord-6e0e7a5aa80541958440505a4a3c7711
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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